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“Why self-advocacy is important.” With Mitch Russo & Ashley Quinto Powell

I’m incredibly passionate about self-advocacy. I speak about salary negotiation for women, I help corporations better support working moms, and I help business owners make the sales that fuel their business. I love to see people make what they’re worth, support their families, and build generational wealth. All of that starts with the ability to […]

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I’m incredibly passionate about self-advocacy. I speak about salary negotiation for women, I help corporations better support working moms, and I help business owners make the sales that fuel their business. I love to see people make what they’re worth, support their families, and build generational wealth. All of that starts with the ability to advocate for yourself in all areas of your life- with your partner, with your boss, with your clients. I’d love for more women to be fantastic advocates, for themselves and other women. We need more women in the C-suite, running 7-figure businesses and balancing work and family in the way that works best for them. Every small shift in that direction is good for the next generation and I’m proud of whatever small part I have in that movement.


As a part of my series about how to be great at closing sales without seeming pushy, obnoxious, or salesy, I had the pleasure of interviewing Ashley Quinto Powell.

Ashley Quinto Powell is a sales and revenue consultant for startups and SMBs. She has worked in technical sales since 2008 and has over $20 million in personal career sales. She is a national speaker — most recently for TEDx, Pinterest and Google — and she supports women in business through formal and informal mentorship communities.


Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to this career path?

Thank you so much for having me! I’ve been in commission-based sales since high school, if you can believe it. I got the best after school job- as a leasing agent at an apartment rental company in downtown Chicago. It taught me so much about sales and working with people. In my early 20s, I founded a tech startup and built out the e-commerce backend. Ultimately, my startup went bust during the recession, but that’s how I got into tech. I went back to work in technical sales at a large consulting firm and built a sales team. After several years of working in a very corporate, very male-dominated company, I started working with smaller tech companies. Now I consult small businesses, many of which are consulting firms, on sales and revenue strategy.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

These days, I speak at conferences for lead generation all the time. It’s a great way to build credibility with potential clients. No one wants to network with a salesperson in the hallway track but everyone wants to network with a speaker. About 5 years ago, I came up with the idea that the brilliant developers I was working with should speak at technical conferences and I would tag along and collect all the leads. But I couldn’t get anyone to apply to speak. I begged and pleaded. Nothing. So I applied to a conference myself and got accepted- really as a way to show my developers how easy it was and goad them into applying. It worked! We developed an incredibly strong speaking strategy. Most of the development staff presented at conferences and helped create a very strong reputation for our little company across the country. I continued speaking all over, and now it’s not only lead generation but a revenue stream all its own. I keynote on topics like salary negotiation and supporting working parents.

Are you working on any exciting new projects now? How do you think that will help people?

I am! My sales strategies have always resonated with people who don’t fit the traditional mold of a salesperson. My clients can’t sell ice to an Eskimo and don’t want to. The Eskimo has plenty of ice. My clients want to provide value. Sales training can be really masculine. It’s one of the reasons my firm exists. Traditional sales programs are built for typical salespeople, who are traditionally young, good looking men with sports backgrounds. That’s pretty alienating to women, people of color… pretty much anyone outside of that box. But we still get sales methodologies with sports and war analogies and a muscle-bound dudebro yelling at us. The scripts recommended by those sorts of programs, (pain funnels, etc.) don’t work for most people- it’s why they come off as salesy. It’s not comfortable and it’s not effective. I’m launching courses so a greater number of business owners can use my methodology and feel confident in their ability to drive revenue for their businesses.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I always credit my husband for this one. (I gave my TEDx talk all about it, actually.) My husband stayed home when our kids were young, which gave my career a chance to really rocket. Having support at home meant I could travel and work long hours and was never called out of a meeting for a sick kiddo or childcare emergency. This is a luxury that many men have had while their wives stay home- but the stay-at-home folks never get the credit they deserve for their spouse’s success.

For the benefit of our readers, can you tell us a bit why you are an authority on the topic of sales?

When I was at large organizations, I was a top performer as an individual contributor and had really successful teams. But when I started working for smaller businesses, I was responsible for all the revenue that came in. All the employee salaries, the owner’s investment, the growth of the company- it all happens because I bring in the sales. Employees will get married and start families because they feel secure in their jobs and they’ll trust the financial security of the company based on the work I do. I love having this responsibility. Today, I consult with business owners about how to do that for themselves.

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the COVID-19 pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

This pandemic will change so much about the world, especially the way we communicate and sell goods and services- but it’s simply a quickening of what has been happening for a long time. In my career, I’ve seen clients become unreceptive to door-to-door sales and cold calling. Our clients don’t want to be stabbed with a business card and given a high-pressure sales pitch. The world has been trending towards a more marketing-driven approach to sales, and smart salespeople have been changing with it. I contend we’ll continue to trend towards relationship-building, knowledge sharing, and collaboration as the world learns to do business in the new normal.

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know, nearly any business a person will enter, will involve some form of sales. At the same time, most people have never received any formal education about how to be effective at selling. Why do you think our education system teaches nearly every other arcane subject, but sales, one of the most useful and versatile topics, is totally ignored?

Great question! I think we have this belief that good salespeople are born, not made. So often, we’ll tell really friendly or talkative people that they’d be great at sales. We think it’s the ability to talk. In reality, it’s the follow-up, ability to listen, think on your feet, to persist, to be tenacious. Those things are harder to teach and harder to grade. Having said that, coursework about how to carry on a good conversation would be a good addition, too!

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesey”, is making an assumption that seeming salesy or pushy is something to be avoided. Do you agree with this assumption? Whether yes, or no, can you articulate why you feel the way you do?

On the one hand, I think it’s critical that our messaging is authentic and feels good. As a rule, if you feel awkward saying it, your client is going to be put off when they hear it. On the other hand, we’re not dating; we’re here to do business. So there’s no reason to dance around difficult questions. For me combining those two sounds like having a great business conversation. It’s not pushy or salesy- it’s just an open and honest conversation.

The seven stages of a sales cycle are usually broken down to versions of Prospecting, Preparation, Approach, Presentation, Handling objections, Closing, and Follow-up. Which stage do you feel that you are best at? What is your unique approach, your “secret sauce”, to that particular skill? Can you explain or give a story?

I’m a Hunter, all the way. Prospecting is where I really shine. I work hard on my personal brand and community involvement so when I reach out to someone, I’m someone they want to know. As part of that, I have created communities of high-performing women in business, partnered with not-for-profits and served on boards. In my initial outreach, I don’t try to sell anything- I just want to get a meeting. And in an initial meeting, I’m trying to build a trusting relationship. I drop enough bread crumbs so that, ideally, my prospect initiates the business part of the conversation.

Lead generation, or prospecting, is one of the basic steps of the sales cycle. Obviously every industry will be different, but can you share some of the fundamental strategies you use to generate good, qualified leads?

The best leads for me are referrals, so I need to make sure I’m top of mind with the folks that will refer me. That usually means being in touch with some regularity and maintaining a decent social media presence. And I pay it forward. A lot. I introduce amazing people to one another as much as I can. Being a good connector is just good business. Clients are inundated with information, so social proof is more important than ever, and the best way to get that is by referral.

In my experience, I think the final stages of Handling Objections, Closing, and Follow-up, are the most difficult parts for many people. Why do you think ‘Handling Objections’ is so hard for people? What would you recommend for one to do, to be better at ‘Handling Objections’?

Getting better at handling objections gets so much better with practice. It’s one of the great arguments for making a lot of attempts. One of my favorite tricks is that if you are consistently getting the same objection, start bringing it up earlier in the conversation- maybe first thing. If you keep getting a price objection, for instance, you might start an initial conversation by bringing it up. “Sometimes people think we’re going to be very expensive, and while there’s an initial investment, our clients have found that the long term benefits make the initial cost well worth it.” By getting it out of the way early, and bringing it up yourself, your client will be far more open to what you have to say.

‘Closing’ is of course the proverbial Holy Grail. Can you suggest 5 things one can do to successfully close a sale without being perceived as pushy? If you can, please share a story or example, ideally from your experience, for each.

-“From my perspective, the next step would be to put contracts in place. What questions can I answer for you before you’re ready for that step?” It’s a great way to move a deal forward.

-If you are authentically excited about working with someone, tell them. I spent too much of my professional life playing it cool; now I make a point of showing how enthusiastic I am about working with a client. It’s flattering and helps build a good rapport.

-I always try to set an appointment for the next step. As part of my process, I have an in-depth meeting to understand the need so I can go back and create a proposal. During the information gathering, I tell them what my proposal is likely to be, what the cost is likely to be, when they can expect it, and I set an appointment for a few days later to talk though questions. Having something set up ahead of time means I don’t have to go chasing my client and my client has a soft deadline to make a decision.

-I make sure a client understands how to tell me ‘no’. I say something like, “I’d love for us to move forward, but if it’s not right for you, I hope you’ll feel comfortable enough to say, ‘I like you, but, this isn’t the right time for us to work together’. When your client knows how to say ‘no’, they don’t ghost you. And you’ve built a better relationship, so if you don’t win this one, you’ll be in the right position to win the business next time.

-A nice, easy way to close is to move the conversation toward what your capacity looks like and what you’re planning for. As a business person, they’ll appreciate that you have to plan and budget time and resources when you take on a new client, so the answers are usually quite candid. “Based on my timeline for the quarter, I can take on a client at the end of this month. Should I save that space for you?” It’s a play on the assumptive close that isn’t tone-deaf the way most assumptive closes can be.

Finally, what are your thoughts about ‘Follow up’? Many businesses get leads who might be interested but things never seem to close. What are some good tips for a business leader to successfully follow up and bring things to a conclusion, without appearing overly pushy or overeager?

In my experience, many leads that aren’t closing is a symptom of not understanding the timing or urgency. Big disconnects between when a client wants to buy and when a salesperson wants a client to buy are major sources of heartache and lost revenue. A strong salesperson won’t, for instance, lower prices at the end of a quarter to drive a few deals to close early. Instead, it’s a good idea to understand your client’s timing, urgency, and budget cycle so you can align your expectations and follow up at the right frequency. Plus, beating up leads like a dead horse is awful and feels terrible. I’d much rather go out and get great, new leads for myself.

As you know there are so many modes of communication today. For example, In-person, phone calls, video calls, emails, and text messages. In your opinion, which of these communication methods should be avoided when attempting to close a sale or follow up? Which are the best ones? Can you explain or give a story?

You should always communicate in whatever mode your client wants to be communicated through. Having said that, I always try to push for the mode that provides the most context. Phone is good, video is better, and in-person is best. I don’t think text or email are the right way to follow up or close- but if that’s the only way I can get ahold of someone, it’ll have to do. Early in my career, I had a client with a big potential deal, who wouldn’t get on the phone to answer my questions, so I gave up and sent my questions by email. It was a disaster. I had asked, maybe, 10 questions. She only answered one of them in her reply and I was basically back where I started.

Ok, we are nearly done. Here is our final “meaty” question. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

Aw, shucks. I’m incredibly passionate about self-advocacy. I speak about salary negotiation for women, I help corporations better support working moms, and I help business owners make the sales that fuel their business. I love to see people make what they’re worth, support their families, and build generational wealth. All of that starts with the ability to advocate for yourself in all areas of your life- with your partner, with your boss, with your clients. I’d love for more women to be fantastic advocates, for themselves and other women. We need more women in the C-suite, running 7-figure businesses and balancing work and family in the way that works best for them. Every small shift in that direction is good for the next generation and I’m proud of whatever small part I have in that movement.

How can our readers follow you online?

You can find me at http://www.ashleyquintopowell.com or on LinkedIn, where I’m very active. I’d love to connect with your readers there. https://www.linkedin.com/in/ashleyquinto/

Thank you for the interview. We wish you only continued success!

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